"Stay Like a Local. Live Like a Boss."
Breathtaking skyline views from a luxurious 3-bed penthouse with private terrace, chef's kitchen, and concierge access.
Elegant townhouse steps from the park. Modern finishes, private patio, and neighborhood charm.
Industrial-chic loft in Chicago's art district. Exposed brick, 14ft ceilings, curated interiors.
Every property is hand-selected and professionally styled. No surprises — just premium spaces that match or exceed the photos.
Smart locks, digital keys, and zero waiting. Arrive on your schedule and walk straight into your haven.
Our curated Chicago guides unlock the city like a local — hidden gems, the best eats, and experiences no travel blog mentions.
Real humans, available around the clock. Restaurant reservations, airport pickups, and anything you need — we handle it.
From the Riverwalk to Michelin-starred dining, from Navy Pier to Wicker Park — Chicago has a pulse that stays with you long after you leave.
Over 20 Michelin-starred restaurants minutes from your door.
World-class museums, galleries, and live music year-round.
Home to some of the world's most stunning skylines and landmarks.
26 miles of lakefront trail, beaches, and Grant Park.
Absolutely spectacular. The penthouse views at night had us speechless. Bossie Stays elevated our anniversary trip to something we'll never forget.
I travel for work constantly, and this was the first short-term rental that felt like a genuine luxury stay. The check-in was seamless and the space was immaculate.
The local guide they sent was worth the entire trip on its own. We found a restaurant that's now our favorite — and no tourist would ever know about it. Bossie is different.
Hand-curated spaces across Chicago's most coveted neighborhoods
Breathtaking skyline views, private terrace, chef's kitchen and concierge access.
Elegant townhouse steps from the park with a private patio and neighborhood charm.
Industrial-chic loft in Chicago's art district. Exposed brick, 14ft ceilings.
Modern flat in Chicago's restaurant row. Open kitchen, premium finishes, walkable to everything.
Artfully designed studio in the most creative neighborhood in Chicago. Perfect for solo travelers.
Historic building, completely reimagined. High ceilings, marble baths, and Magnificent Mile access.
Welcome to the crown jewel of Bossie Stays — a stunning penthouse perched above The Loop with 270° panoramic views of the Chicago skyline and Lake Michigan.
This 1,800 sq. ft. masterpiece features a chef's kitchen with Sub-Zero appliances, a private wraparound terrace, three elegantly appointed bedrooms, and spa-worthy bathrooms with rain showers and soaking tubs. The interiors are designer-curated — warm neutrals, statement lighting, and art pieces sourced from local Chicago galleries.
Everything you need is steps away: Millennium Park, the Riverwalk, fine dining on Randolph Street, and world-class architecture in every direction.
"One of the best stays of our lives. The views at night were unreal."
"Immaculate property, seamless check-in. Will book every Chicago trip."
You won't be charged yet · Free cancellation 48h before
Every stay is backed by our satisfaction guarantee. If anything doesn't match the listing, we'll make it right — immediately.
The story of a young entrepreneur redefining how Chicago is experienced
Bossie Stays was born from a simple belief: every traveler deserves a home that feels like it was designed just for them — not a sterile hotel room, not a random apartment, but a thoughtfully curated space that combines the comfort of home with the luxury of a high-end hotel.
Founded by a young Chicago entrepreneur who saw a gap between budget short-term rentals and true luxury experiences, Bossie Stays was built to bridge that gap — with premium properties in Chicago's most coveted neighborhoods, curated local guides, and a hospitality standard that makes you feel like royalty from check-in to check-out.
Hotel-grade linens, premium appliances, and spaces you'll never want to leave.
We're Chicagoans. Every recommendation, every neighborhood tip — it's genuinely local.
What you see is what you get, and then some. No hidden fees, no surprises.
"Building something bigger than myself — one stay at a time."
I'm a Chicago-based entrepreneur and college football player who believes that discipline on the field translates directly into excellence in business. Balancing athletics and building a company from the ground up has sharpened my focus, leadership, and relentless attention to detail — and those are the exact qualities I pour into every single Bossie Stays property.
I've always been driven to create something of my own. Bossie Stays is that vision made real — a business built on the belief that every traveler deserves a space designed with intention, comfort, and style. Not just a place to sleep, but a place to experience the city the right way.
Have questions about a property, need a custom arrangement, or want to partner with us? We're here.
Chicago, Illinois
Serving the greater Chicagoland area
[email protected]
Response within 2 hours
+1 (312) 000-0000
Available 7am – 10pm daily